The present invention relates to a novel cyclic phenol sulfide sulfonic acid compound, which can be used as a metal scavenger, an ion sensor, a separation membrane material, a substrate-specific sensor, a phase-transfer catalyst, an artificial enzyme, a light energy conversion material or an intermediate of a functional molecule capable of recognizing an ion or a molecule.
Furthermore, the present invention relates to a process for producing sulfonic acid of a cyclic phenol sulfide and a salt thereof, in which an alkyl group is directly replaced with a sulfonic group by reacting a cyclic alkylphenol sulfide with sulfuric acid.
Moreover, the present invention relates to a recovery agent and a recovery process of an organic halogen compound or a monocyclic aromatic compound which is deleterious in the living environment and the like, and relates to a novel agent for recovering an organic halogen compound or a monocyclic aromatic compound, which comprises a cyclic phenol sulfide, and a process for recovering an organic halogen compound or a monocyclic aromatic compounds by bringing the organic halogen compound or the monocyclic aromatic compound into contact with the cyclic phenol sulfide.
Also, the present invention relates to a medicament which uses a cyclic phenol sulfide as an active ingredient and to a composition comprising the same. More particularly, it relates to an antiviral agent, especially an anti-HIV agent having activity for retrovirus, such as HIV (human immunodeficiency virus) and the like.
Novel cyclic phenol sulfides completely different from the conventionally known non-cyclic phenol sulfide have been found, and a process for producing such cyclic phenol sulfides has also been found (JP-A-9-227553).
These cyclic phenol sulfides include a compound having a sulfonic group at the p-position on the benzene ring based on the hydroxyl group. However, in order to produce cyclic phenol sulfide sulfonic acid to which a sulfonic group is introduced at the p-position of the benzene ring based on the hydroxyl group, it is necessary to employ two step reactions for once carrying out dealkylation of a cyclic alkylphenol sulfide by replacing the alkyl group with a hydrogen atom and then sulfonating it using fuming sulfuric acid or the like, so that a high production yield cannot be expected and its production sometimes requires a prolonged period of time.
Also, environmental pollution by organic halogen compounds including trihalomethanes and the like whose carcinogenicity has been pointed out and monocyclic aromatic compounds, such as phenol and the like, becomes a problem in recent years, so that their effective elimination processes have been expected.
For example, organic halogen compounds, such as 1,1,1-trichloroethane and the like, are broadly used mainly as detergents in industries, such as automobile, electronic, electric, precision instrument, and the like, but cause serious problems regarding environmental pollution due to that they flow into rivers through contaminated waste water from factories or the compound once evaporated into the air is mixed with rain water and contaminate underground water and soil. Additionally, so-called trihalomethanes, such as chloroform, dibromochloroethane and the like, are contained in tap water as disinfection by-products of tap water and well known as carcinogenic substances as described above. Carcinogenicity of benzene regarded as one of air pollutants has also been pointed out.
With regard to these organic halogen compounds and monocyclic aromatic compounds, such as benzene and the like, their respective regulated values are specified by the water environment standard, as well as the water pollution control law and effluent standard, water supply law and water quality standard of tap water, sewage water law and sewage water effluent standard, and soil environment standard.
Additionally, among monocyclic aromatic compounds, for example, phenol can be regarded as a cause of water pollution due to that there is a possibility that a small amount of underground water and the like is contaminated in industrial waste water and soil.
A process for recovering contaminants can be exemplified as an important process for solving such environmental pollution. Accordingly, research and development have been attempted on various separation recovery techniques, such as membrane separation techniques, extraction techniques, and the like, but concern has been directed toward a pollutant recovering process which is more efficient, an energy-saving type, inexpensive, and easy to handle.
AIDS (acquired immunodeficiency syndrome) is now world-widely considered to be one of the greatest threats which spoil human life and health. The number of AIDS patients reported to WHO (the World Health Organization) until the end of December, 1994 is 1,020,000, but it is said that its actual number is assumed to be approximately 4,500,000, and it is said also that the number of infected people reaches 4 to 5 times of the actual patients.
Accordingly, studies on the AIDS virus, namely HIV, are actively carried out with various objects, such as elucidation of the origin of HIV and its structure including gene structure of the virus, elucidation of the infection route, protection of infection, diagnosis, treatment, prevention of infection, and the like.
HIV contains RNA as the gene, and belongs to retrovirus which breaks into a host and transcripts its genetic information from RNA to DNA by a reverse transcriptase to the opposite direction of ordinary transcription. The HIV-concerning infection cycle has been fairly elucidated.
Consequently, studies have been carried out actively on the development of anti-AIDS agents considered to have effects on respective steps of the infection cycle. That is, the anti-HIV agents include an adsorption inhibitor, an uncoating inhibitor, a reverse transcription inhibitor, an integration inhibitor, a transcription translation inhibitor, an HIV protease inhibitor and the like. Peptide polymer substances considered to have a neutralization activity and sulfated polysaccharides considered to have an activity to coat virus particles physically have been developed as the adsorption inhibitor; cyclic polyamine compounds as the uncoating inhibitor; and nucleoside compounds, such as AZT and the like, and non-nucleoside compounds, such as TIBO compound and the like, as the reverse transcription inhibitor.
However, the anti-HIV agents have serious problems still unsolved, namely strong side effects, such as neurological disorder, organ function disorder, and the like, and their high expression frequency and generation of respective resistant strains after prolonged period of administration.
Recently, development of protease inhibitors has been carried out actively. While the reverse transcription inhibitor inhibits HIV-DNA formation, the protease inhibitor inhibits processing of HIV constitutive protein. Accordingly, use of both inhibitors in combination can inhibit the copying of virus by the protease inhibitor which have not been inhibited by the reverse transcription inhibitor, so that their high combined effect is expected.
However, even in the case of the protease inhibitor, side effects, such as lipemia and the like, have been pointed out so that it is not free from the problem of side effects, and it also has a problem of being considerably expensive as a drug.
That is, a substantially inexpensive drug which is superior in anti-HIV activity and the like, causes less side effects and can be produced by a simple and easy production process is desired.
An object of the present invention is to provide a cyclic phenol sulfide sulfonic acid compound represented by formula (1).
Also, an object of the present invention is to provide a process for producing sulfonic acid of a cyclic phenol sulfide, and a salt thereof, in which the alkyl group of a cyclic alkylphenol is directly replaced with a sulfonic group using sulfuric acid as a sulfonation agent at a high yield, efficiently and easily.
Furthermore, an object of the present invention is to provide, in a technique for recovering organic halogen compounds or monocyclic aromatic compounds which are typical environmental pollution substances, a separation recovery agent which has a conventionally unknown and completely new structure and has excellent recovery capacity of an organic halogen compound or a monocyclic aromatic compounds, and a separation recovery process.
Moreover, an object of the present invention is to provide a medicament, particularly an antiviral agent, which has an antiviral activity, is low in cytotoxicity, can be produced by an easy and simple process, and is inexpensive.
That is, the present invention relates to a sulfonic acid compound of a cyclic phenol sulfide represented by formula (1): 
(wherein X represents a hydrogen atom, a hydrocarbon group, or an acyl group;
M represents a hydrogen atom, an alkyl group, a metal, an ammonium, a (lower-alkyl)ammonium, a (lower-alkanol)ammonium, a nitrogen-containing heterocyclic group, or an amino acid residue;
Z represents Sm, SO, or SO2;
m is an integer of from 1 to 7; and
n is an integer of from 4 to 12,
with the proviso that the plural X""s, M""s and Z""s are each the same or different, and at least one of the plural M""s is neither a hydrogen atom nor an alkyl group).
Furthermore, the present invention relates to a process for producing sulfonic acid of a cyclic phenol sulfide or a salt thereof, comprising reacting a cyclic alkylphenol sulfide represented by formula (2): 
(wherein Y1 represents an alkyl group, and Z and n have the same meanings as defined above) with sulfuric acid to produce sulfonic acid of a cyclic phenol sulfide represented by formula (3): 
(wherein Z and n have the same meanings as defined above), or a salt thereof.
Moreover, the present invention relates to a composition for separating and recovering an organic halogen compound or a monocyclic aromatic compound, which comprises a compound represented by formula (4): 
(wherein X, Z and n have the same meanings as defined in formula (1);
Y represents a hydrogen atom, a hydrocarbon group, a halogenated hydrocarbon group, xe2x80x94COR1, xe2x80x94OR2, xe2x80x94COOR3, xe2x80x94CN, xe2x80x94CONH2, xe2x80x94NO2, xe2x80x94NR4R5, a halogen atom, xe2x80x94SO4R6, xe2x80x94SO3R7, or xe2x80x94SO3M;
R1 to R7 are a hydrogen atom or a hydrocarbon group; and
M has the same meaning as defined in formula (1),
with the proviso that the plural X""s, Y""s and Z""s are each the same or different), or a salt thereof, and a carrier.
Also, the present invention relates to a process for separating and recovering an organic halogen compound or a monocyclic aromatic compound, comprising bringing a compound represented by formula (4) or a salt thereof into contact with an organic halogen compound or a monocyclic aromatic compound to separate and recover the organic halogen compounds or the monocyclic aromatic compound.
Still furthermore, the present invention relates to a composition which comprises a compound represented by formula (4) or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier or diluent.
Still moreover, the present invention relates to use of a compound represented by formula (4) or a pharmaceutically acceptable salt thereof for prevention or treatment of a disease caused by a virus production.
Additionally, the present invention relates to a process for preventing or treating a disease caused by a virus production, comprising administering an effective amount of a compound represented by formula (4) or a pharmaceutically acceptable salt thereof to a human or an animal (e.g., mammals).
Still additionally, the present invention relates to a process for selectively inhibiting a virus production, comprising administering an effective amount of a compound represented by formula (4) or a pharmaceutically acceptable salt thereof to cells.